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Updated: Apr 16, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Direct ortho-C-H functionalization of aromatic alcohols masked by acetone oxime ether via exo-palladacycle
Kun Guo1, Xiaolan Chen1, Mingyu Guan1
1Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry, Chemical Engineering and Materials Science Soochow University, Suzhou 215123, PR China.
Abstract:
A simple and practical exo-oxime ether auxilixary for ortho-C-H functionalization of aromatic alcohols has been developed. Selective olefination of aromatic alcohols were first achieved via a six- or seven-membered exo-acetone oxime ether palladacycle with broad substrate scope. In addition, the crystal of the exo-palladacycle intermediate was obtained for the first time, and the application of this method in total synthesis of 3-deoxyisoochracinic acid was accomplished via a novel retro-synthetic disconnection approach, thus demonstrating the utility of this transformation.
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